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$2,415,000
8 Beds ⋅ 5 Baths ⋅ 202603590 MLS ⋅ FS - Fee Simple Tenure ⋅ 130 DOM
Enjoy best of Kailua living, sunshine & breezes, in coveted Kalaheo Hillside. This multigenerational home offers a perfect harmony of connection and independence, designed for a lifestyle where everyone has a place to call their own. Unique side-by-side wings (6/3 and 2/2) provide separate private retreats for extended family or guests, with versatility. Rich wood floors in the living room and expansive primary suite create an atmosphere of warmth and modern elegance, with luxury vinyl plank and tile floors throughout the rest of the home. Enjoy a backyard oasis created for making memories, featuring a sparkling tiled pool and multiple covered and open lanais for golden hour gatherings or quiet tropical nights. Perched on a prominent corner lot, on a peaceful, friendly street, it’s just blocks from the soft sands of Kailua’s world-class beaches. With the convenience of Aikahi Shopping Center dining, shopping, coffee & banking, nearby MCBH facilities, desirable schools and parks, this is more than a house- it’s a lifestyle decision. You’ll appreciate options for seamless access to H-3, Kam, Likelike, and Pali highways for best commute possible. Bedroom count doesn’t match TMK.

304 Ilimano Street, Kailua
$2,310,000
4 Beds ⋅ 3 Baths ⋅ 202611972 MLS ⋅ FS - Fee Simple Tenure ⋅ 52 DOM
Tucked onto one of Kalaheo Hillside's most sought-after streets, 445 Iliwahi Loop is a fully reimagined 4-bed, 3-bath retreat blending timeless island architecture with a clean, considered renovation — vaulted ceilings, an open great room flowing to covered lanais, and walls of glass framing the pool, gardens and fountains. This generous lot sits against the conservation hillside adding to the peace and quiet of this location. The chef's kitchen pairs a Viking range and Sub-Zero refrigeration w/a generous island open to the dining & living areas. Two primary suites suit multigenerational living or a guest wing, the spa-inspired primary bath w/a soaking tub and oversized shower. Two additional bedrooms w/shared bath PLUS 2 office/flex rooms Outside is your own resort: a sparkling pool (plus spa hookup), mature landscaping, a garden gazebo and covered lanai seating for golden-hour gatherings. NEM metering, 2 Tesla Powerwalls, + a new GACO roof! Freshly painted inside & out, new flooring, lighting & fans throughout. Minutes to Kailua Beach, a short hop to Marine Corps Base Hawaii, and moments from H-3, Pali and Likelike — with Aikahi Shopping Center and dining close at hand.

445 Iliwahi Loop, Kailua
$2,229,100
4 Beds ⋅ 4 Baths ⋅ 202606138 MLS ⋅ FS - Fee Simple Tenure ⋅ 52 DOM
Island luxury abounds in this newer-built single-family residence in Kailua. Very privately situated, and tucked behind a gated driveway, the CPR home welcomes you with expansive parking and 2+ car garage. Soaring ceilings and open entry foyer set the tone for a light-filled, spacious interior. The open-concept living area features built-in entertainment center and flows seamlessly to a covered lanai, where tranquil canal views and sunrise hues create a serene daily backdrop over the lush landscaping. A chef’s kitchen is appointed with quartz, high end appliances, gas, and a decked out indoor butler pantry/laundry area, perfect for entertaining and everyday living. Upstairs, the primary suite is a peaceful retreat with huge walk-in closet and a glass-enclosed shower, dual vanities. Two additional bedrooms, and hallway bath with tub. A separate downstairs bedroom suite with exterior access, full bath, and walk-in closet provides flexibility for guests, multigenerational living, or a private workspace. LVP flooring, quality craftsmanship and thoughtful design complete this exceptional opportunity to enjoy modern Kailua living indoor and out, your personal paradise.

1142 Mokapu Boulevard, Kailua
$2,190,000
4 Beds ⋅ 3 Baths ⋅ 202614657 MLS ⋅ FS - Fee Simple Tenure ⋅ 45 DOM
This is the one you have been waiting for! This home, in the desirable Kalaheo Hillside neighborhood, is strategically positioned on a large 10,000 sq. ft. lot to allow the cool ocean breezes to flow through. Large front windows overlook a welcoming tropical garden. There’s something for everyone! A large gourmet kitchen, open floor plan, sparkling tiled pool, indoor laundry, attached garage with workshop area, 4 bedrooms and three full bathrooms. Included in the 4 bedrooms is a studio with private entrance, kitchen, washer/dryer and ensuite bathroom totally separate from the rest of the house! Room for all and great for multi-generational living or long-term rental income. Ideally located with close proximity to Aikahi elementary school, Kalaheo High School, Aikahi Shopping Center, Kaneohe Marine Corp Base, H-3, Kailua Beach and mere minutes from Kailua town. Outside, a shower is conveniently located for washing off the beach sand and toys. The grounds surrounding the house are filled with beautiful Hawaiian flora, green grass lawn and mango, avacado and starfruit trees. On a quiet night you can even hear the sound of the breaking waves!

361 Iliaina Street, Kailua
$2,160,000
4 Beds ⋅ 3 Baths ⋅ 202520664 MLS ⋅ FS - Fee Simple Tenure ⋅ 55 DOM
Fall in love with Kailua living in this beautiful home with luxury upgrades in the highly desirable Kalaheo Hillside neighborhood. The open floor plan and spacious layout with vaulted ceilings invite light and connection, seamlessly flowing into the living and dining areas creating the perfect gathering space. Appreciate the modern kitchen with quartz countertops, white cabinetry, and stainless steel appliances with luxury vinyl plank flooring and split AC throughout, providing both luxury living and comfort. The spacious yard invites outdoor gatherings also offering the potential for a legal ohana unit with included architectural plans. Perfectly situated for ocean lovers, this home is just minutes from Kailua Beach, Kaneohe Bay, and Kaneohe Yacht Club perfect for surfing, paddling, sailing, or simply enjoying the turquoise waters. The prime location offers everyday convenience with Aikahi Shopping Center, Kaneohe Marine Base, and quick access to H-3. This home enjoys access to schools including Aikahi Elementary, Kailua Intermediate, and Kalaheo High. Experience the best of island living where comfort, convenience, and coastal lifestyle come together in one exceptional home.

323 Iliaina Street, Kailua
$1,975,000
4 Beds ⋅ 2 Baths ⋅ 202523645 MLS ⋅ FS - Fee Simple Tenure ⋅ 76 DOM
There’s something special about a home that feels like your own little escape. This 4 bedroom, 2 bath property was thoughtfully remodeled to blend timeless modern design with the laid-back ease of island living. Set on just over 10,000 square feet of land, the property features a large freeform pool. Coconut palm and a Ma‘afala (breadfruit) tree add a touch of tropical beauty to the setting while the fenced yard provides privacy plus a nice place for children and pets to play. A large skylight in the open kitchen offers a bright space to create nourishing dishes. Sparkling bathrooms feature upgraded fixtures, a walk-in shower, tub, and washlets. You will love having your own EV charging station, garage with storage, and split air conditioning. This location offers easy access to H-3, Kailua town, and Kaneohe. With 36 owned PV panels, two Tesla wall batteries, a solar water heating system, and DPP-ready plans for an ADU plus garage -- this is an easy choice. Natural light, clean lines, and warm finishes make every corner feel intentional and inviting. If indoor-outdoor living is your thing, come see why this could be for you!

319 Iliaina Street, Kailua
$1,915,000
6 Beds ⋅ 5 Baths ⋅ 202524371 MLS ⋅ FS - Fee Simple Tenure ⋅ 47 DOM
SAY WHAAAAT?? 4,000 square feet under roof and almost 2,000 square feet of lanais--in a prized Kailua neighborhood--UNDER $2-million? You know you'd better come running! Perfect combination of space, style, and opportunity await you. With 3 distinct living areas, this home is ideal for extended family, guests, or rental income. The upper-level 3 bed/2 bath ohana offers stunning ocean and mountain views. The lower level includes a 2 bed/2 bath suite and a 1 bed/1 bath unit—each with its own generous lanai and private washer/dryer. You'll appreciate the abundant storage throughout and off-street parking for up to seven cars. HECO bills are kept to a minimum with 34 NEM PV panels and solar water heat, and the whole property is fenced and fire sprinklered for your safety! Ideally located near top-rated Aikahi Elementary and Kalaheo High schools, MCBH, commute lanes, and the white sands of Kailua Beach’s famed Castles surf break. This is a rare opportunity to live, work, and thrive in one of Oahu’s most desirable communities. SOMEONE is going to celebrate the New Year in this extraordinary home. Maybe you? CALL YOUR AGENT NOW! We expect to present offers on Thursday, 11/6, at 10 AM.

443 Iliaina Street, Kailua
$1,600,000
3 Beds ⋅ 2 Baths ⋅ 202614057 MLS ⋅ FS - Fee Simple Tenure ⋅ 35 DOM
Welcome home to this spacious three-bedroom, two-bathroom residence in the highly sought-after Kalaheo Hillside. Freshly painted along with other upgrades throughout, this Kailua home offers a seamless blend of modern comfort and island charm. The open-concept interior is designed for indoor-outdoor living, leading you towards the large, flat fully-enclosed backyard oasis framed by lush tropical landscaping—a perfect backdrop for weekend gatherings or quiet afternoons in the sun. Situated just a short walk Castles Beach and the convenience of Aikahi Shopping Center, this location puts everything Kailua has to offer at your fingertips. Located within the Aikahi school district and just minutes to the vibrant dining and boutique shopping of Kailua town, this property captures the relaxed, active lifestyle you’ve been looking for.

923 Mokapu Boulevard, Kailua
$1,600,000
4 Beds ⋅ 3 Baths ⋅ 202520868 MLS ⋅ FS - Fee Simple Tenure ⋅ 78 DOM
Exempted Listing.

525 Ilimano Street, Kailua
$1,505,000
4 Beds ⋅ 2 Baths ⋅ 202515758 MLS ⋅ FS - Fee Simple Tenure ⋅ 58 DOM
Located in the highly desirable Kailua beach community, this spacious mid-century modern, single-level home offers 1,828 square feet of relaxed island living. Designed with an open-concept layout, open beam ceilings, the interior features brand-new LVP flooring and fresh interior and exterior paint is a move-in ready. The fully fenced yard provides both privacy and space for outdoor living, while a solar water heater adds energy efficiency. Just minutes from world-renowned beaches, shopping, and dining. Home is sold “As Is.” Bedrooms and bath are virtually staged.

339 Ilimalia Loop, Kailua
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 202601018 MLS ⋅ FS - Fee Simple Tenure ⋅ 40 DOM
Discover the perfect blend of comfort, convenience, and island living in this spacious, well-maintained 3-bedroom, 3-bath home located in the highly sought-after Aikahi School District. The open floor plan creates an inviting and flexible living space, ideal for entertaining family and friends or simply relaxing at home. Set on a generous 9,900 sq ft lot, this home embraces indoor-outdoor living with an enclosed backyard and covered lanai - perfect for weekend barbecues, playtime with kids and pets, or enjoying your morning coffee. The two-car carport offers seamless access to the kitchen for effortless daily living and includes lockable storage closets to keep everything organized. Conveniently located near Pali Highway, Likelike Highway, and H-3, you're just minutes from top-rated schools, shopping, dining, and Kailua's world-famous white sand beaches. Enjoy the convenience and charm of single-level living in one of Kailua's most desirable locations.

1209 Mokapu Boulevard, Kailua
$1,100,000
4 Beds ⋅ 2 Baths ⋅ 202519838 MLS ⋅ FS - Fee Simple Tenure ⋅ 39 DOM
Centrally located 4 bedroom, 2 bathroom home with a port cochere & 2 covered parking stalls on Kalaheo Hillside could be your next home or investment. Enjoy a spacious covered lanai off the back of the house & refurbish the pool to your heart’s desire. Walk sought after school districts, Aikahi Park Shopping Center & dining. Minutes to Kaneohe Marine Corps Base, Kailua Beach, Lanikai Beach, & freeway access, this home is conveniently located. Seller is offering a credit of up to 2.5% toward Buyer’s closing costs.

1104 Mokapu Boulevard, Kailua

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.